2-Methyl-2-butene → HCID 66682626, compound

HRID 1964608Notes

Reaction equation

HRID 1964608 reaction equation
[F:1][C:2]1[CH:35]=[C:34]([CH:36]=[O:37])[CH:33]=[CH:32][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([C:17]2[NH:21][C:20]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[CH:19][CH:18]=2)[CH:8]=[C:9]([O:11][C@@H:12]([CH3:16])[CH2:13][O:14][CH3:15])[CH:10]=1.O.O.P([O-])(O)(O)=[O:41].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>[Cl-].[Na+].O.O.C(O)(C)(C)C>[CH2:25]([O:24][C:22]([C:20]1[NH:21][C:17]([C:7]2[CH:6]=[C:5]([CH:10]=[C:9]([O:11][C@@H:12]([CH3:16])[CH2:13][O:14][CH3:15])[CH:8]=2)[O:4][C:3]2[CH:32]=[CH:33][C:34]([C:36]([OH:41])=[O:37])=[CH:35][C:2]=2[F:1])=[CH:18][CH:19]=1)=[O:23])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 86649568HCID 86649568, compound

Product 1

HCID 66682626HCID 66682626, compoundYield 109.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Benzyl 5-{3-(2-Fluoro-4-formylphenoxy)-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-1H-pyrrole-2-carboxylate (6.33 g, 12.6 mmol) synthesized in Example (66d) was suspended in a mixed solvent of t-butanol (120 mL) and water (40 mL), and sodium dihydrogen phosphate dihydrate (8.86 g, 56.8 mmol) and 2-methyl-2-butene (12.05 mL, 113 mmol) were added. Under ice cooling, sodium chlorite (80%, 2.93 g, 25.9 mmol) was added slowly, and stirring was carried out at room temperature for 2 hours. Saturated brine (200 mL) was added, followed by extraction with dichloromethane (200 mL), and drying was carried out over anhydrous magnesium sulfate to afford the desired compound (7.17 g, yield ˜100%) as a pale yellow oil.

Workup

  1. additionwere added
  2. extractionfollowed by extraction with dichloromethane (200 mL)
  3. customdrying

Sources & evidence

ORD record
ord-bb8967a184734e018e89ef6bfe01a254
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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